What We Can Learn From Successful Entrepreneurs

What challenges do we really face when we start our own small businesses, and how can we overcome them? What does it take to make the leap of faith? And what are the rewards of being entrepreneurs?

I have been interviewing successful entrepreneurs for my blog, Yes to Me. So far, I have posted ten articles for this series, interviewing thirteen entrepreneurs (three posts feature a pair of entrepreneurs). These are small business owners who have built profitable businesses that resonate with who they are. Most are bloggers, or at least have web presence, but their businesses vary greatly, from internet marketing to pet insurance company. They include men, women, young, older.

Are there common traits among these entrepreneurs? I think so. This article reviews their answers to two of my standard questions and explores the theme among them so that we can learn from the mistakes and victories they have so gracefully shared with us.

What were the biggest challenges when you were starting as new entrepreneurs?

Lack of money, lack of sales / marketing expertise and self-doubt are the top three challenges they site, followed by lack of business plans, management issues regarding the employees and business partners, time management and multi tasking, and more.

Depending on the business, the capital it takes differs, but even for a one-person operation, money is a challenge. Some of my interview guests mentioned what it was like to bootstrap, and I’m guessing even the ones who didn’t mention it probably went through similar challenges.

The issue of money gets aggravated by the lack of sales and marketing expertise. Many new entrepreneur have the technical skills of their trade but not the sales skill to bring their products and services in front of their target customers in an effective way. They struggle to define their target clients (Stephen) and to find the right pricing (Susanna). They may not have many contacts to network (Monica). Harry says, “We had the skills and the business knowledge we needed, but we knew very little of bringing this to the virtual world.”

Self-doubt is a biggie that holds back many aspiring entrepreneurs, and it continues to interfere many even after they take the plunge. Christine says “I didn’t think I was good enough.” Jason says “it’s easy to start second-guessing yourself. ‘Am I crazy?’ seemed to be a recurring question that popped up in my head.”

How can we turn around the lack and get over our fear?

Christine says the lack of money actually worked favorably for her. She says “I had tried to start businesses on the side for years, but because I didn’t NEED them to succeed, they didn’t. When I quit my job and had no other options, I knew that I was either going to have to make it, or else.” She used the lack to motivate her and to stay focused.

Skip advises “Cash is king in a startup. Yet focusing on fund-raising has never been a favorite approach of mine. I’d rather ‘bootstrap’, demonstrate that I can get clients and build value without an investor.”

Sales takes a lot of courage and footwork. Lack of money, and therefore the naked need to promote our businesses, helps new entrepreneurs to gather the courage and to be humble enough to learn the new skill of sales and marketing. James says “Being an entrepreneur is more than just working on your own for a living. You suddenly wear many hats and you suddenly have to be an expert at everything, from salesperson to customer service representative . . .”

And so is getting over self-doubt. There is never a complete assurance. Business is an ongoing challenge, and even successful entrepreneurs have self-doubt from time to time. However, successful entrepreneurs put their fear aside and keep moving forward because they know the rewards outweigh the fear.

What is the best part of being an entrepreneur for you?

While my interview guests point out various challenges in entrepreneurship, they agree on the rewards of entrepreneurship. They may use different words, but they pretty much boil down to three points: Freedom, Confidence, Contribution.

Most of my interview guests mention the freedom to use their time in the way they see best, the freedom to do what they like and do well. Tony says “freedom is the driving force . . . I love being able to work when I choose. I also love being successful enough to turn down work I don’t want . . .” He goes on to express his view of freedom and responsibility saying “If I have to work for an idiot, I may as well work for myself”

The confidence comes by actually overcoming difficulties. As entrepreneurs, we come to realize we can really do what we vision. James says “Knowing that we are able to reach any goal we want and having the confidence to do so is the best feeling in the world.” We open up to the level of possibilities we didn’t know before. Christine says “The best part about being an entrepreneur is that you can see so many more possibilities in business and in life. Suddenly, anything really is possible.”

Being able to help others, the sense of contribution to the community through work and beyond, is also essential for many entrepreneurs. Many of them started their businesses to help others, and the sense of contribution is by itself one of the biggest rewards for them. Laura says “It’s such a cliché but it comes down to being able to build something from nothing that solves people’s problems. There’s no feeling like it.”

How can we make the leap to entrepreneurship?

I’d like to wrap up this article by quoting what Naomi had to say. “I read in a magazine once that you should never be 100{54c12dad2cc2b53ae830e39915b1a3e70288dbcbbeb8bbf8395437c5dc3c512c} ready to have kids. If you think you’re 100{54c12dad2cc2b53ae830e39915b1a3e70288dbcbbeb8bbf8395437c5dc3c512c} ready, you’re missing something. I think the same thing applies to business. If you wait until you’re 100{54c12dad2cc2b53ae830e39915b1a3e70288dbcbbeb8bbf8395437c5dc3c512c} ready, you’ll be dead before you launch. Be 80{54c12dad2cc2b53ae830e39915b1a3e70288dbcbbeb8bbf8395437c5dc3c512c} ready. Do the best you can and just go for it.”

Business is really like a baby for the entrepreneur. We need to prepare well for the challenges, and there is a point we need to jump if we are serious about having one. I hope this article serves to inspire and inform you in your journey to successful entrepreneurship.

List of posts in the Interview With Successful Entrepreneurs series at Yes to Me:

Are you a successful or an aspiring entrepreneur? We would love to hear you thoughts regarding this article in the comments section below.

Akemi Gaines writes for Yes to Me – Life Purpose, Entrepreneurship, Spiritual Growth. She is a new entrepreneur herself, serving people who are serious about personal and spiritual growth through her coaching and soul (Akashic Record) reading. You can subscribe to her blog here.

The Interview With Successful Entrepreneurs series is ongoing and Akemi is always looking for quality interview guests. Please check this page and contact her if you are interested.

Image by Ordinary Guy.


Erin shows overscheduled, overwhelmed women how to do less so that they can achieve more. Traditional productivity books—written by men—barely touch the tangle of cultural pressures that women feel when facing down a to-do list. How to Get Sh*t Done will teach you how to zero in on the three areas of your life where you want to excel, and then it will show you how to off-load, outsource, or just stop giving a damn about the rest.

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